Simple and efficient asymmetric synthesis of furofuran lignans yangambin and caruilignan A

被引：15

作者：

Mori, N

Watanabe, H

Kitahara, T

机构：

[1] Univ Tokyo, Grad Sch Agr & Life Sci, Dept Appl Biol Chem, Bunkyo Ku, Tokyo 1138657, Japan

[2] Kitasato Inst, Ctr Basic Res, Lab Nat Prod Chem, Minato Ku, Tokyo 1088642, Japan

来源：

SYNTHESIS-STUTTGART | 2006年 / 03期

关键词：

asymmetric synthesis; oxidative dimerization; furofuran lignan; yangambin; caruilignan;

D O I：

10.1055/s-2006-926271

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel asymmetric dimerization of cinnamic acid derivative was achieved in high efficiency and high stereoselectivity. By using the reaction as a key step, two furofuran lignans, yangambin and caruilignan A were synthesized in optically pure form in only 5 and 6 steps, respectively.

引用

页码：400 / 404

页数：5

共 50 条

[1] An efficient asymmetric synthesis of furofuran lignans: (+)-sesamin and (-)-sesamin
Kim, JC
Kim, KH
Jung, JC
Park, OS
TETRAHEDRON-ASYMMETRY, 2006, 17 (01) : 3 - 6
[2] Synthesis of furofuran lignans
Brown, RCD
Swain, NA
SYNTHESIS-STUTTGART, 2004, (06): : 811 - 827
[3] A NOVEL ASYMMETRIC-SYNTHESIS OF AXIAL-EQUATORIAL FUROFURAN LIGNANS - A SYNTHESIS OF (+)-FARGESIN
YOSHIDA, S
YAMANAKA, T
MIYAKE, T
MORITANI, Y
OHMIZU, H
IWASAKI, T
TETRAHEDRON LETTERS, 1995, 36 (40) : 7271 - 7274
[4] Synthesis and antioxidant activity of oxygenated furofuran lignans
Yamauchi, S
Ina, T
Kirikihira, T
Masuda, T
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2004, 68 (01) : 183 - 192
[5] DIASTEREODIVERGENT CHIRAL SYNTHESIS OF THE FUROFURAN LIGNANS (+)-SESAMIN AND (-)-ASARININ
SAMIZU, K
OGASAWARA, K
CHEMISTRY LETTERS, 1995, (07) : 543 - 544
[6] Electochemical asymmetric dimerization of cinnamic acid derivatives and application to the enantioselective syntheses of furofuran lignans
Mori, Naoki
Furuta, Akiko
Watanabe, Hidenori
TETRAHEDRON, 2016, 72 (51) : 8393 - 8399
[7] Stereoselective total synthesis of furofuran lignans through dianion aldol condensation
Jung, Jae-Chul
Kim, Ju-Cheun
Moon, Hyung-In
Park, Oee-Sook
TETRAHEDRON LETTERS, 2006, 47 (36) : 6433 - 6437
[8] Stereoselective Synthesis of Lignans of Three Structural Types from a Common Intermediate, Enantioselective Synthesis of (+)-Yangambin
Syed, Majid Khalil
Murray, Cian
Casey, Mike
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (25) : 5549 - 5556
[9] ASYMMETRIC-SYNTHESIS OF LIGNANS
WARD, RS
TETRAHEDRON, 1990, 46 (15) : 5029 - 5041
[10] INTRAMOLECULAR ENE-BASED APPROACH TO FUROFURAN LIGNANS - TOTAL SYNTHESIS OF NEOPAULOWNIN
MIKAMI, K
MATSUEDA, H
NAKAI, T
SYNLETT, 1993, (03) : 235 - 236

← 1 2 3 4 5 →